IP Library Granted Patent US 11,274,189
Granted Patent B2
US 11,274,189 · App. 16/583,802 · Granted Mar 15, 2022

Curing agents for compounds

Inventors: Christopher J Bish (Kennett Square, PA); Peter A Morken (Wilmington, DE); Amiya Ratan Tripathy (Garnet Valley, PA)
Assignee: DuPont Polymers, Inc.
C08K5/31C08K3/04C08K5/405
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Quick Facts
Patent No.
US 11,274,189
App. No.
16/583,802
Granted
Mar 15, 2022
Kind
B2
Abstract

Curing fluoroelastomers using curing agents of formula, R 1 N═CR 2 R 3 , wherein R 1 is H; R 2 is selected from the group consisting of H, NH 2 , and NR 4 R 5 ; R 3 is selected from the group consisting of Ph, SO 2 H, NR 6 R 7 , 2-pyridine, and CH 2 CONH 2 ; R 4 is H; R 5 is selected from the group consisting of Ph, NH 2 , and CN; R 6 is selected from the group consisting of H, NHPh, CCONH 2 , C 1 to C 8 linear alkyl group, and C 1 to C 8 branched alkyl group; and R 7 is selected from the group consisting of Ph, COOC(CH 3 ) 3 , NH 2 , CH 2 COOH, CSNH 2 , CNHNH 3 + Cl − , p-phenylCN, COPh,

Claims (30)

1. A compound comprising:

A. a fluoroelastomer comprising copolymerized units of:

(1) one or more unsaturated fluorinated olefins;

(2) one or more unsaturated fluorinated olefin co-monomer different from 1) selected from the group consisting of fluorovinyl ethers, unsaturated fluorinated olefins, unsaturated olefins, and mixtures of these; and

(3) one or more cure site monomers selected from the group consisting of nitrile-containing fluorinated olefins and nitrile-containing fluorinated vinyl ethers; and

B. 0.1 to 10 mole percent of at least one curing agent of formula (I):

R 1 N═CR 2 R 3   (I)

wherein:

R 1 is H;

R 2 is selected from the group consisting of, NH 2 , and NR 4 R 5 ;

R 3 is selected from the group consisting of, SO 2 H, NR 6 R 7 , 2-pyridine, and CH 2 CONH 2 ;

R 4 is H;

R 5 is selected from the group consisting of, NH 2 , and CN;

R 6 is selected from the group consisting of H, CCONH 2 , and

R 7 is selected from the group consisting of, COOC(CH 3 ) 3 , NH 2 , CH 2 COOH, CSNH 2 ,

CNHNH 3 + Cl − , p-phenylCN, COPh,

provided that when R 7 is CSNH 2 , R 2 is not NH 2 .

2. The compound of claim 1 , further comprising 0.1 to 5 phr of a curing agent C different from curing agent B.

3. The compound of claim 1 , wherein the unsaturated fluorinated olefin (a)(1) is selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, 1,1-difluoroethylene; 1,1,2-trifluoroethylene; 1-fluoroethylene, and mixtures of these.

4. The compound of claim 2 , wherein the unsaturated fluorinated olefin (a)(1) is selected from the group consisting of tetrafluoroethylene, hexafluoropropylene, 1,1-difluoroethylene; 1,1,2-trifluoroethylene; 1-fluoroethylene, and mixtures of these.

5. The compound of claim 3 , wherein the unsaturated fluorinated olefin co-monomer (a)(2) is selected from the group consisting of perfluoro(methyl vinyl) ether, hexafluoropropylene, perfluoro(propyl vinyl) ether, and mixtures of these.

6. The compound of claim 4 , wherein the unsaturated fluorinated olefin co-monomer (a)(2) is selected from the group consisting of perfluoro(methyl vinyl) ether, hexafluoropropylene, perfluoro(propyl vinyl) ether, and mixtures of these.

7. The compound of claim 1 , wherein the curing agent B is selected from the group consisting of amidinoamidine HCl, phenyloxoaminoamidine, 3-(5-phenyl-4H-1,2,4-triazolyl)amidine, 1H-pyrrolylamidine, benzimidazolylamidine, aminothioxoamidine; aminocarbonylmethylamidine HCl, N-aminoamidine bicarbonate, N″-1H-pyrazolyl-N′-t-butoxycarbonylamidine, 2-pyridylamidine HCl, sulfinoamidine, and mixtures of these.

8. The compound of claim 5 , wherein the curing agent B is selected from the group consisting of amidinoamidine HCl, phenyloxoaminoamidine, 3-(5-phenyl-4H-1,2,4-triazolyl)amidine, 1H-pyrrolylamidine, benzimidazolylamidine, aminothioxoamidine; aminocarbonylmethylamidine HCl, N-aminoamidine bicarbonate, N″-1H-pyrazolyl-N′-t-butoxycarbonylamidine, 2-pyridylamidine HCl, sulfinoamidine, and mixtures of these.

9. The compound of claim 8 , further comprising at least one filler selected from the group comprising nonperfluoro-fluorine-containing elastomers, micropowders, carbon black, stabilizers, plasticizers, lubricants, processing aids, and mixtures of these.

10. The compound of claim 2 , wherein the curing agent C is selected from the group consisting of organotin curing agents, bis(aminophenol) curing agents, bis(aminothiophenol) curing agents, tetraamine curing agents, triamine curing agents, diamine curing agents, and mixtures of these.

11. The compound of claim 2 , wherein the curing agent B is selected from the group consisting of amidinoamidine HCl, phenyloxoaminoamidine, 3-(5-phenyl-4H-1,2,4-triazolyl)amidine, 1H-pyrrolylamidine, benzimidazolylamidine, aminothioxoamidine; aminocarbonylmethylamidine HCl, N-aminoamidine bicarbonate, N″-1H-pyrazolyl-N′-t-butoxycarbonylamidine, 2-pyridylamidine HCl, sulfinoamidine, and mixtures of these.

12. The compound of claim 10 , wherein the curing agent B is selected from the group consisting of amidinoamidine HCl, phenyloxoaminoamidine, 3-(5-phenyl-4H-1,2,4-triazolyl)amidine, 1H-pyrrolylamidine, benzimidazolylamidine, aminothioxoamidine; aminocarbonylmethylamidine HCl, N-aminoamidine bicarbonate, N″-1H-pyrazolyl-N′-t-butoxycarbonylamidine, 2-pyridylamidine HCl, sulfinoamidine, and mixtures of these.

13. The compound of claim 6 , wherein the curing agent B is selected from the group consisting of amidinoamidine HCl, phenyloxoaminoamidine, 3-(5-phenyl-4H-1,2,4-triazolyl)amidine, 1H-pyrrolylamidine, benzimidazolylamidine, aminothioxoamidine; aminocarbonylmethylamidine HCl, N-aminoamidine bicarbonate, N″-1H-pyrazolyl-N′-t-butoxycarbonylamidine, 2-pyridylamidine HCl, sulfinoamidine, and mixtures of these.

14. The compound of claim 13 , further comprising at least one filler selected from the group comprising nonperfluoro-fluorine-containing elastomers, micropowders, carbon black, stabilizers, plasticizers, lubricants, processing aids, and mixtures of these.

Assignments (5)
NUNC PRO TUNC ASSIGNMENT Recorded Nov 6, 2025
From: DUPONT POLYMERS, INC.
To: DUPONT SPECIALTY PRODUCTS USA, LLC
Reel/Frame 072805/0695 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: JPMORGAN CHASE BANK, N.A., AS COLLATERAL AGENT
Reel/Frame 073515/0243 →
SECURITY INTEREST Recorded Nov 3, 2025
From: QNITY ELECTRONICS, INC.
To: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 073517/0298 →
NUNC PRO TUNC ASSIGNMENT Recorded Sep 6, 2024
From: DUPONT POLYMERS, INC.
To: DUPONT POLYMERS, INC.
Reel/Frame 068512/0400 →
CHANGE OF ADDRESS Recorded Sep 6, 2024
From: DUPONT POLYMERS, INC.
To: DUPONT POLYMERS, INC.
Reel/Frame 068859/0287 →